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Full text of "Preliminary tests of some phenol esters of butyric acid"

LIBRARY 
STATE PLANT BOARD 

May 1954 



E-877 



United States Department of Agriculture 
Agricultural Research Service 
Entomology Research Branch 



PRELIMINARY TESTS OF SOME PHENOL ESTERS OF EUTYRIC ACID 
S. I. Gertler and A. P. Yerington 



Thirty-four phenol esters of butyric acid were tested as insec- 
ticides in the laboratory of this Branch at Anaheim, Calif., from 
December 1951 to April 1952. These compounds may be represented by 
the general formula 



CoH'7— C-CR 

where R is a phenyl, substituted phenyl, or naphthyl group. These com- 
pounds were prepared by reacting the phenol with butyric anhydride under 
suitable conditions. These compounds were tested against three species 
of insects and one mite. 

The following species were used: 

Armyworm ( pseudaletia unipuncta (Haw.)) 

Large milkweed bug ( Oncopeltus fasciatus (Dall.)) 

Pea aphid ( Macrosiphum pisi (Harris)) 

Two-spotted spider mite ( Tetranychus bimaculatus Harvey) 

The insects were reared in the laboratory, and the two-spotted 
spider mites were collected in the field. 

In each test that a given species was used, the following number of 
individuals were tested: 30 larvae of the armyworm, 20 milkweed bugs, 
from 25 to 1*0 adult pea aphids, and from tiO to 60 adults of the two- 
spotted spider mites. For the armyworm, foliage was sprayed and then 
placed in petri dishes for the larvae to feed upon. Large milkweed 
bugs were placed in 8-cm. crystallizing dishes and sprayed; after treat- 
ment, they were provided with clean water and food. The adult pea 
aphids were removed from an infested plant and sprayed, and then placed 
on untreated, potted Windsor bean plants in cloth-capped glass battery 
jars for the observation period. The two-spotted spider mites were 
sprayed while on castor bean leaves and were held in battery jars. 

The compounds, tested as acetone sprays against all species, were 
applied with a Potter spray tower. Sprays were first tested at a J>- 
percent concentration on a weight /volume basis, and if a mortality of 



- 

90 percent or higher resalted the COI ^ 

, . A single • 

nt . 

Disc 

■ 
beet, 
cent water e 
v to the test rlants. The 

3l caused sei to ai: 

.tachlorophenol 
tomato; moderate injury to pumpkin; ge . 

»t sore of the re* 1 . : ^ncentrat nese COBJ 

are effective, it might be possible for then to be .- . 

In order to show the effect of chemical stru re on U 
of the compounds to these pests, the data an U 

with the compounds arranged in order of desce re- 

sults for d spray are included in each table. 

In the test the third-ins tar la: X the - 

e 1), it is it the butyric acid ester- -hly 

S^»* Wtized.by the Internet Archive; " 

somewhat less so, richlono. orHO 

to 100 percent kjipjl £\)\0 

off compl- -percent. phenol es 

than the chloro ester. -o-cre 

• jcic but • what less so than the 

The ate of o-n 

n the | 

. 

see 

e estf 

cres 

... 
ion of 

the o- 

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■ 

http://archive.org/details/prbulystsOOunit 

Al 



- 3 - 

phenols only the 2-naphthol ester showed some toxicity. 

Table 3 shows that approximately half of the compounds at the 
5-percent concentration resulted in over 90-percent kill against the 
adult pea aphids. Here a rather mixed pattern is noted. The dinitro 
derivatives were still the most toxic, with the p_-nitrophenol ester 
slightly less so. The trichloro and tribromophenol esters and the tet- 
rachloro compound were among the more effective compounds. However, 
among the compounds giving the higher kill the esters of the naphthoxs 
the cyclohexyl phenols, and some mixed substituents with halogen tert- 
butyl groups are noted. It is also noteworthy that £-nonylphenol 
butyrate, which appears near the bottom of the first two tables, is 
among the more toxic compounds against the pea aphid. In fact it showed 
greater kill than the lower aliphatic substituents. The pentachloro- 
phenol ester, which was most effective against the armyworm, was prac- 
tically nontoxic to the pea aphid. 

In the tests against the adult two-spotted spider mite (table h) , 
it is interesting to note that all the compounds showed 100-percent 
kill at 5-percent concentration and more than half showed at least 90- 
percent kill at 1-percent. The pentachloro, tetrachlorc, and the two 
dinitro substituted phenols head the list, and seemed to be quite effec- 
tive miticides. The other highly halogenated compounds were also some- 
what more toxic than those containing less halogen. Here again the 
cyclohexyl and p-nonyl derivatives were among the more effective com- 
pounds . 

Of all the compounds tested, li,6-dinitro-o-cresol butyrate was the 
most toxic, showing a high kill on all test insects down to 1-percent 
concentration and being a good miticide at 0.05>-percent. The 2,U-dini- 
trophenol ester was also effective against all four insects, though only 
moderately toxic to the armyworm. The ester of pentachlorophenol was 
also an effective miticide and the most toxic of the compounds tested 
against the armyworm. 

On the whole, it is evident that most of the compounds demonstrated 

no consistent effect on all the test animals. In some compounds almost 

a complete reversal was noted in the relative effectiveness of the com- 
pounds to different test species. 



- 1 - 



it kill of third-ins" r f tin 

ent vrl .s concentrations of 

in acetone solution.^/ 



Butyric acid ester of-- 



nt 


1 percent 


percent 


IOC - 


100 


_ 


XX 


- 


^3 


x 


7 xx 


- 


73 


X 




- 


7 


xxx 




- 




X 




- 





XX 




IX - 





XX 




IOC' - 





xxx 




- 





xxx 




IOC - 





xxx 




- 




xxx 




98 - 





xxx 




x 









X 





X 




90 x 




XX 




9C 





xxx 




90 - 





xxx 




PC x 





xxx 




x 




XX 




87 - 








73 xx 








67 








60 xx 








60 xx 








60 xx 








53 








50 








XX 








hO xxx 
















XX 








XXX 








7 xxx 









Phenol, pentachloro- 

. , . ,6-tetrachloro- 
• sol, r.itro- 

m-Cresol, 6-ter 1- 

nol, 2, .' hloro- 

0-C: 
o-isopi 
, ,'-':■: Icro- 
c-Cresol, - oro- 
nol, 2,Ii-dichloro- 
o-nitro- 
p-ethyl- 
p-Cresol _ 
Phenol, m-cthyl- 

p-tert-tutyl- 
£-isopropyl- 
o-Cresol 

nol, p-chloro- 
£-Cresol, 2-t tyl- 

Phenol, 2,J.-dinitro- 

l.-tert-butyl-2-chloro- 
n-Cresol 
o-Crescl, L -tert -butyl - 

•omo-|.-tert-but;. 
o-cyclohexyl- 
p-bromo- 

, . -tribromo- 
p-cyclohexyl- 

ithol 

tiyl- 

. - 'hlcrf 

. 1 - 



xxx 



DDT 









• ■ . 



-5 - 



Table 2. — Percent kill of fourth-ins tar nymphs of the large milkweed 
bug 2 days after treatment with various concentrations of butyric 
acid esters in acetone solution 



Butyric acid ester of — 



5 1 0.5 0.1 

percent percent percent percent 



Phenol, 2,li-dinitro- 


100 


100 


90 


o-Cresol, U,6-dinitro- 


100 


100 


65 


Phenol, p_-tert-butyl- 


100 


5 




p-isopropyl- 


100 







p_-nitro- 


95 


Uo 




2-Naphthol 


70 






o-Cresol, h-chloro- 


60 






Phenol, £-bromo- 


55 






2 , k , 5- 1 ri chlor o- 


UO 






p-ethyl - 


25 






2,3jh,6-tetrachloro- 


20 






1-Naphthol 


20 






Phenol, m-ethyl- 


15 






£-chloro- 


15 






m-Cresol 


10 






6-tert-butyl- 


10 






p_-Cresol,2-tert-butyl- 


10 






Phenol, 2-bromo-li-tert-tutyl- 


10 






£-cyclohexyl- 


10 






o-nitro- 


10 






2 , Ii , 6-tri chlor o- 


5 






p_-Cresol 


5 






o-Cresol, U-tert-butyl- 


5 






Phenol, 2,ii-dichloro- 


5 






pent achloro- 


5 






li-tert-butyl-2-chloro- 


5 






o-Cresol 









Phenol, 2-brorao-h-phenyl- 









o-chloro- 









o-cyclohexyl- 









2 , U-dic hloro-6-phenyl- 









o-isopropyl- 









p_-nonyl- 









2 , h ,6-tribromo- 










50 



Lindane (0.005 percent) 



91 



- 6 - 



Table 3. — Percent kill of adult pea arhids 2 days after treat»i>ent with 
various concentrations of butyric acid esters in acetone solution 



Butyric acid ester of-- 



5 percent 1 percent 9 $ percent 



o-Cresol, u,6-dlnitro- 


100 


■ 


Phenol, 2,!i-dinitro- 


100 




p_-nitro- 


100 


55 


2,Li,5-trichloro- 


100 




p -nonyl- 


100 


22 


2-Naphthol 


100 


19 


phthol 


100 


US 


Phenol, p_-cyclohexyl- 


100 


US 


2-bromo-li-tert-butyl- 


100 


13 


o-cyc lohexyl- 


100 


10 


Ti-t ert-butyl-2-chloro- 


ICO 


10 


2,14,6-tribronc- 


100 


7 


o-Cresol, h-tert-butyl- 


100 




P*henol, 2,1,6-trichloro- 


9L 




m-ethyl- 


93 




2, 3,!i,6-tetrachloro- 


01 


35 


p-broino- 


88 




2-bromo-!:-phenyl- 






2,h-dichloro- 


81 




o-Cresol, h-chloro- 


76 




Phenol, p_-tert-tutyl- 


75 




o-chloro- 


75 




p_-isopropyl- 


68 




p-Cresol, 2-tert-butyl- 


59 




Phenol, 2,li-dichloro-6>-phenyl- 


^Q 




p-ethyl- 


53 




m-Cresol"7 6-tert-tutyl- 


51 




p-Cresol 


37 




resol 


27 




Phenol, o-lsopropyl- 


27 




m-Cresol 


111 




Phenol, o-ni t.ro- 


9 




pentachloro- 


5 




p-chloro- 


o 





58 



Parathion (0.005 percent) 






- 7 - 



Table U. — Percent kill of adult two-spotted spider mites 2 days after 
treatment with various concentrations of butyric acid esters in 
acetone solution 



Butyric acid ester of — 



$% 1.0£ 0.5% O.lg 0.05* 0.0l£ 0.00& 



Phenol, pentachloro- 

2,U-dinitro- 
o-Cresol, li,6-dinitro- 
Phenol, 2,3,l*,6-tetrachloro- 

p-cyclohexyl- 

2,l;,5-trichloro- 

p-nonyl- 

2,U,6-tribromo- 

2,li,6-trichloro- 

p_-nitro- 

o-cyclohexyl- 

2 -bromo-it-ter t -butyl- 

p_-chloro- 

2 ,h-dichloro-6-phenyl- 

m-ethyl 
o-Cresol, U-chloro- 
Phenol, o-chloro- 
g-Cresol, 2 -ter t-butyl- 
phenol, 2,i;-dichloro- 

o-isopropyl- 

2 -bromo-li-phenyl- 

p-isopropyl- 
m-Cresol 

o-Cresol, U-tert-butyl- 
1-Naphthol 

m-Cresol, 6-tert-butyl- 
2-Naphthol 
Phenol, h-tert-butyl-2-chloro- 

£-tert-butyl- 
o-Cresol 
Phenol, p-ethyl- 

p-bromo- 
P_-Cresol 
Phenol, o-nitro- 



100 




100 


100 


100 


tt 


100 




100 


100 


93 


56 


100 




100 


100 


91 


76 


100 




100 


100 


he 




100 


93 


96 


26 






100 


100 


91 


5 






100 


100 


88 


10 






100 


96 


92 









100 


100 


78 








100 


93 


7U 








100 


100 


60 








100 


92 


51 








100 


100 


31 








100 


100 


19 








100 


93 


12 








100 


91 


8 








100 


93 


a 








100 


90 


7 








100 


8U 










100 


83 










100 


81 










100 


71 










100 


66 










100 


66 










100 


6U 










100 


61 










100 


61 










100 


iiU 










100 


39 








- 


100 


33 










100 


27 










100 


18 










100 


17 










100 


16 











51 



Parathion (0.005 percent) 



89 



3 1262 09240